Water → 8-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo(1,2-a)pyridine

HRID 1762220Notes

Reaction equation

HRID 1762220 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:8]([CH2:12][C:13]#[CH:14])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[K].[CH3:16][O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23]Cl)=[O:19].O>CN(C)C=O>[CH3:16][O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23][O:1][C:2]1[C:3]2[N:4]([C:8]([CH2:12][C:13]#[CH:14])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 5462222PotassiumHCID 143683478-Hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridineHCID 143684802-Methyl-6-methoxycarbonylaminobenzyl chloride

Product 1

HCID 1952178-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo(1,2-a)pyridineYield 6.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-hydroxy-2-methyl-3-(2-propynyl)imidazo[ 1,2-a]pyridine (0.372 g) and potassium carbona (0.276 g) in N,N-dimethylformamide (7.4 ml) was stirred at room temperature for 20 minutes under a nitrogen atmosphere and then 2-methoxycarbonylamino-6-methylbenzylchloride (0.427 g) was added. After being stirred for 2 hours. The mixture was poured into water and the resulting precipitates were collected by filtration. The crude product was purified by column chromatography on silica gel (10 g) with chloroform as eluents to give 8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (0.048 g).

Workup

  1. stirringAfter being stirred for 2 hours
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. customThe crude product was purified by column chromatography on silica gel (10 g) with chloroform as eluents

Sources & evidence

ORD record
ord-d5df752a92ee41baa4ad1fbd0269297a
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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